Upcoming Events
There’s always something happening at Inn at Perry Cabin, and we invite you to be part of it. From waterfront gatherings and seasonal celebrations to relaxed moments that unfold throughout the day, our calendar brings people together in ways that feel easy, social, and genuinely enjoyable on Maryland’s Eastern Shore.
Settle in for open-air evenings like Summer Cinema on Linden Lawn, or step into experiences with a sense of occasion, from celebratory feasts to thoughtfully curated dinners. Holiday weekends bring their own energy, with Memorial Day, the Fourth of July, and Labor Day filling the property with outdoor events, live music, and moments that invite you to linger a little longer.
Whether you’re planning ahead or looking for things to do in St. Michaels, you’ll find a rhythm here that feels welcoming, lively, and worth saying yes to.
Summer
Enjoy a Garden Tour
Join us on Wednesdays and Saturdays at 10:30 AM for a guided, horticulturist-led tour designed to share insight into our gardens, seasonal plantings, and landscape design. Learn what’s in bloom, how it’s cared for, and what makes each season unique. Reservations are recommended, as select dates may be unavailable.
Discover Seasonal Garden Highlights
Tours are open to both Inn guests and day visitors, with pricing at $25 per person for non-hotel guests.
Summer Cinema on Linden Lawn
*Films subject to change based on licensing.
Rum Running on the Skipjack
Join us every Wednesday, June - August, from 5:30–7:00 PM for an evening of sailing, storytelling, and handcrafted tastings from our friends at LYON Rum . This adventure is timed perfectly to catch a front-row view of the Wednesday Night Sailboat Races on the Miles River. Learn more on our Fleet page, or contact Concierge Team at 443-258-2228 or [email protected].
Labor Day Weekend
Toast to the final days of summer with a festive waterfront weekend.
Friday, September 4
3–6 PM | Live Acoustic Music Nina Peterson
Waterfront Terrace
Veuve Clicquot, Rosé & Sancerre
Harris Creek Oysters with Pickled Watermelon & Garden Mint Relish
Saturday, September 5
12 - 3 PM | Live Music Patty Reese
The Pointe
Upscale Crush Bar, Beer & Wine
Wood-Fired Pizza & Roasted Summer Bites
Sunday, September 6
12–3 PM | Live Acoustic Music Justin Ryan
The Pointe
Red, White & Blue Cocktails, Beer & Wine
Eastern Shore BBQ Featuring Slow-Roasted Chicken, Smoked Pulled Pork & BBQ Shrimp
Fall
Chesapeake Film Festival
The prestigious Chesapeake Film Festival returns to Easton, Maryland from October 8th - 10th! Immerse yourself in the magic of cinema with a captivating lineup of acclaimed films, thought-provoking documentaries, and engaging discussions with industry experts.
Fall into St. Michaels
Fall into the enchantment of St. Michaels October 17th! Experience the charm of our scenic town as it comes alive with scarecrow contests, pumpkin pie eating competitions, and pumpkin carving festivities scattered throughout. Immerse yourself in the vibrant spirit of the season as you wander the streets adorned with whimsical creations.
Haunted Tales of St. Michaels
Join us on Wednesdays and Saturdays at 2:30 PM throughout October for a guided walk through the haunted history of Inn at Perry Cabin and St. Michaels. Hear tales of local legends, lost lovers, witches and spirits as you explore historic homes and inns with stories spanning centuries.
Reservations and additional details coming soon.
Halloween Harvest Festival
October 31 | 12 PM – 4 PM
Celebrate the season with a festive afternoon of live music, autumn treats, family-friendly activities, and fall fun throughout the grounds. From pumpkin picking and costume contests to seasonal food and unexpected surprises, there's something for guests of all ages to enjoy.
Stay tuned for additional details and event programming.
Trick-or-Treat in St. Michaels
Keep the Halloween fun going in town as Talbot Street and the surrounding neighborhoods come alive with costumed trick-or-treaters. Local shops, businesses, and neighbors join in, welcoming families with plenty of treats and small-town Halloween spirit. More Details Coming Soon.
Historic Drawbridge Running Festival
On October 31st, take on one of Maryland’s flattest courses with a 5K, half marathon, or marathon through beautiful Talbot County. The marathon and half marathon begin on Tilghman Island, crossing historic drawbridges on the way toward St. Michaels, while the 5K starts and finishes right next door at the Chesapeake Bay Maritime Museum. Learn More & Register
Oyster Fest
Get ready to indulge in the flavors of the Chesapeake Bay's favorite fall festival! Join us for Chesapeake Bay Maritime Museum’s Oyster Fest on Saturday, November 7th for a day filled with live music, exciting retriever demonstrations, and of course, mouthwatering oysters and more. Sip on local brews, slurp down freshly shucked oysters, and savor the taste of autumn by the bay. It's an event you won't want to miss!
Waterfowl Festival
Experience the charm of the Eastern Shore at Easton's Waterfowl Festival, taking place from November 21st! Delight in a weekend filled with exquisite art collections, culinary delights, and the authentic ambiance of the Chesapeake Bay. Immerse yourself in the rich tradition of waterfowl calling and witness captivating live demonstrations. Don't miss this true Eastern Shore classic, where art, culture, and nature converge for an unforgettable celebration!
Eastern Shore Sea Glass & Coastal Arts Festival: Holiday Edition
Mark your calendar for November 22nd, as the Chesapeake Bay Maritime Museum in St. Michaels, Maryland, hosts the Holiday Edition of the beloved Sea Glass and Coastal Arts Festival. This seasonal celebration will showcase coastal craftsmanship at its finest, with over 90 exhibitors offering unique jewelry, home décor, art, and more—just in time for the holidays.
A Time to Gather
Gather around our table this Thanksgiving. Join us from 12–5 PM for an abundant spread specially prepared for the occasion, bringing family and friends together for a memorable afternoon at Perry Cabin.
Reservation details coming soon..
Annual Lighting of the Lane
Celebrate the start of the holiday season as Inn at Perry Cabin comes aglow for our annual Lighting of the Lane. Join us on Friday, November 27 for an evening of holiday cheer as we light the lane and welcome a special jolly visitor.
Additional details coming soon.
Winter
Wreath Making Workshops
A little greenery, a little creativity and plenty of holiday cheer. Join us at Inn at Perry Cabin to create a wreath of your own to take home for the holiday season. Classes will be held December 5, 12, 18 & 19 from 3–5 PM.
Pricing and reservations details coming soon.
Christmas Eve at STARS
The lights are glowing, the halls are decked and Christmas is just around the corner. Settle in at STARS Restaurant for a festive Christmas Eve and a three-course prix fixe dinner featuring traditional Christmas fare. Dinner will be served from 5:30–9 PM.
Reservations and additional details coming soon.
Christmas Day at STARS
Make Christmas Day one to linger over at STARS Restaurant. Enjoy a three-course prix fixe menu accompanied by the sounds of live piano for a festive afternoon at the Inn. Christmas Day dining will be offered from 1–7 PM.
Reservations and additional details coming soon.
